Chloral derivatives containing the radical of a fatty acid.



- pharmaceutical action placed by an arylinstance, when using theethyl-amid of NATHAN SULZIBERGER, or NEW Yuan, n. Y.

CHLORAL DERIVATIVES CONTAINING THE RADICAL OF A FATTY ACID.

No Drawing.

Specification of Letters Patent.

ltatented hilay 7, 1912.

Application filed April 20, 1909. Serial No. 491,162.

To all whom it may concern Be it known that I, NATHANSULZBERGER, acitizen of the United States of America, residing at No. 34 WestSeventy-first street, New York city, in the county of New York and Stateof New York, have invented new and useful Improvements in ChloralDerivatives Containing the Radical of a Fatty Acid, of which thefollowing is a specification.

My invention relates to new compounds containing chloral in combinationwith the amids and derivatives and mixtures of same with fatty acidscontaining more than twelve atoms of carbon and derivatives and mixtures of same. These compounds are taste-' less and odorless, readilysplit up, especially with caustic alkalis, nonvolatile andnonhygroscopic. They can be dissolved in. fats, oils, etc., of mineral,vegetable and animal origin. and be used in such shape especially asointments, salves, soaps, etc., for the skin. Into such ointments, etc.,other chemicals of may be mixed. These new compounds are made bydissolving the amid or mixtures, or derivatives of such amid or mixtureof derivatives of such amids in chloralbest used in excess. Ondistilling off the excess of chloral or freeing the formed compound insome other way from such excess of chloral, the new bodies are obtained.They may be recrystallized from alcohol, etc., if further purificationis desired. The general formula of these compounds is the following:

where 'X stands for the radical of a fatty acid, having more than twelveatoms of carbon or a derivative of such acid, and Y stands for hydrogenor an alkylor arylgroup, which latter new compounds containing analkylor aryl-group are obtained, it instead of the fatty acid amid, afatty acid amid was used, one of whose atoms of hydrogen of the amidogroup, had been reor alkyl-group, as for stearic acid. While for lack ofa suitable generic term including both an alkyland an aryl-group as wellas hydrogen I have limited the claims to products containing an alkylgroup, I nevertheless consider as of the new compound equivalentsthereof products containing such an aryl group as well as productscontaining hydrogen in place of the alkyl group. As a sample of oneofthese compounds, I give the following formula, made by dissolvingalpha-bromstearic acid anilid in chloral:

As an example, I shall describe the preparation of the new chloralderivative with the amid of palmitic acid.

The amid of palmitic acidmade by dropping palmitic acid chlorid intostrong ammonia or prepared in any other wa vis dissolved with gentleheat in somewhat more than one molecular proportion of chloral, 18 gramsfor instance of the amid may be dissolved in about 12 grams (about 10gr. theory) of chloral. Gradually the temperzn ture is raised to about100 degrees C. The light yellow liquid while yet warnii and in an oilyfreed from the excess of chloral. The new compound separates outimmediately in hard white lumps which are freed from the water and maybe recrystallized from dilute alcohol. The pureproductcl1.loral-palmitic acid amid-is a white crystalline powder offatty feel, tasteless and odorless, non-hygroscopic, soluble in alcohol,etc., and fats and,

Oils. It can be kept indefinitely without changing and melts at 110degrees C. A

determination of nitrogen showed it to have the composition abovewritten(0.1935 grams contained (at 17 de grees and 770 mm.) 5.6 ccm. nitrogenor 3.39%, while the theory demands 3.49%.)

Commercial fatty acids-as for instance such are obtained by saponifyinganimal and vegetable fats and oils-may be used in making thesecompounds. Lanolin, parafiin, vas'line, benzoinated lard, etc, can beused in making selves, etc. Other chemicals of desirable pharmaceuticalaction may be mixed in.

I claim: 1. As new compositions of matter the herein described.compounds of chloral with condition is poured into water and thus amidsof fatty acids, suchfiacias olitaihixig' ,more than twelve atomsof-carbom. having tl 1 e following general formula:

suchnompounds' binig ih'soluble' 111 water and not volatile withm'ltdecomposition.

2.' A s a new coixlfiositiqn of matter the chlordlQpaImitic-acid amidbeing a white Crystalline pqwder of fatty fe'el, not vo1a--- 15 tile,meltin at about 110 degrees C.,' and soluble in a cohoI and having thefollowing structural formula Cl 11 c1-c-on K u- K I 0( m :cm- NATHANSULZBERGER. Witnesses: I

R. CHRISTIANSEN,

LEWIS E. Bnmsm'.

Gopica' of b'e (qbtiafiinei! ioi'flve' cents each, by addresing tlie vcbl nhllssioner 'of Patents,

